Share this:

Art by Shy Cabajar

I remember back in 2007 when Martin Scorsese finally won the Oscar for Best Director that it felt more like a Lifetime Achievement Award than truly winning for The Departed. It didn’t feel like the right place or the right time moment for Scorsese. As joyous as it was to see the beloved director finally win, it left some questioning whether it was too little, too late?

I had that same fear the moment I saw the trailer for The Revenant with every Vulture and Gawker proclaiming, “This is it! This is when Leo will finally win his Oscar!” The trailer did seem promising, but I wasn’t readying the confetti just yet — this was still an Alejandro González Iñárritu film we were talking about. After seeing The Revenant, I realized — the second right after that god-awful last scene — that Leo shouldn’t win. Not for this. Not this year.

Don’t get me wrong, I love Leo and have been a fan of most of his work. But The Revenant wasn’t his best by far, and certainly not worthy of the award. If we’re talking about great performances in that film, it was actually Tom Hardy who stole the show more than anyone else in that cast did. But that’s a story for another day.

As this year’s Oscars played on, Leo’s win loomed more and more, and I just kept thinking that this was Martin Scorsese circa 2007 all over again. The excitement had fizzled, and it seemed that everyone across the world already had their “Congrats, Leo!” tweets ready, just waiting to be sent across social media. This was their win too, after all. It was the people who started this whole uproar every time Leo lost. They wanted this win so bad and they knew, like everyone else did, that it was finally going to be their year.

“DiCaprio the poster boy for so many who’ve been rejected, even if in reality, Leonardo DiCaprio is the complete opposite of a rejected loser. So with Leo finally winning, now that he has everything he’s ever wanted in his career, what’s next for him?”

There’s nothing more boring than a sure win, and that’s what Leo was this year. His road to the Oscars was nothing short of formulaic. He looked at recent Oscar winners and realized that the Academy loved characters who were suffering, a time-honored tradition from Sean Penn in I Am Sam and Charlize Theron in Monster to Eddie Redmayne in The Theory of Everything and Julian Moore in After Alice. And it was then that Leo realized that for him to become the best, he would have to suffer as much as he could. He worked with Iñárritu, the most insufferable director today. He shot in the coldest, harshest place in the world, and endured all sorts of things involving animals. It didn’t matter what he had to do, as long as it got him closer and closer to that acceptance speech.

When he finally won, the crowd immediately stood up in unison and gave him a standing ovation. Social media spewed out every celebratory gif for Leo as if they had all practiced this dance their entire lives. It felt rehearsed, replacing excitement for something expected.

It always bothered me that this whole campaign for Leo portrayed him as an everyman to so many people, the beloved underdog who tried as his hardest but just kept on losing year after year. But Leo is the total opposite of an underdog. He was never short of anything to win an Oscar. He had the entire backup of Hollywood’s best; he didn’t lack a devoted fan base who’d support his films. It’s only because of his losses that has made DiCaprio the poster boy for so many who’ve been rejected, even if in reality, Leonardo DiCaprio is the complete opposite of a rejected loser. So with Leo finally winning, now that he has everything he’s ever wanted in his career, what’s next for him? Will the world love him just as much or will we finally realize that Leo was never the unlucky underdog, that he was always the King of the World, and we just gave him what he kept demanding from the world every year, whether he deserved it or not.

My mentor always told me that he fears praises more than criticism, and that’s what I feel about Leo’s win. Now that he’s finally won, what else is there for him to do? What else is there for us to connect with him? Throughout the years, he’s tried so hard to reach the top, spent so much effort to be the best, and did everything he could to win. And now that he’s won, does he realize what he’s actually lost?